Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

S. M. Biros; E. C. Ullrich; F. Hof; Laurent Alain Claude Trembleau; J. Rebek Jnr

doi:10.1021/ja038823m

Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

S. M. Biros, E. C. Ullrich, F. Hof, Laurent Alain Claude Trembleau, J. Rebek Jnr

Chemistry

Research output: Contribution to journal › Article › peer-review

98 Citations (Scopus)

Abstract

We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

Original language	English
Pages (from-to)	2870-2876
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	126
DOIs	https://doi.org/10.1021/ja038823m
Publication status	Published - 2004

Keywords

MOLECULAR RECOGNITION
AQUEOUS-MEDIA
SYNTHETIC RECEPTORS
AMMONIUM CATIONS
CAVITANDS
INCLUSION
GUEST
ACETYLCHOLINE
CHEMOSENSOR
DERIVATIVES

Access to Document

10.1021/ja038823m

Cite this

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title = "Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity",

abstract = "We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.",

keywords = "MOLECULAR RECOGNITION, AQUEOUS-MEDIA, SYNTHETIC RECEPTORS, AMMONIUM CATIONS, CAVITANDS, INCLUSION, GUEST, ACETYLCHOLINE, CHEMOSENSOR, DERIVATIVES",

author = "Biros, {S. M.} and Ullrich, {E. C.} and F. Hof and Trembleau, {Laurent Alain Claude} and {Rebek Jnr}, J.",

year = "2004",

doi = "10.1021/ja038823m",

language = "English",

volume = "126",

pages = "2870--2876",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

AU - Biros, S. M.

AU - Ullrich, E. C.

AU - Hof, F.

AU - Trembleau, Laurent Alain Claude

AU - Rebek Jnr, J.

PY - 2004

Y1 - 2004

N2 - We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

AB - We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. H-1 NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

KW - MOLECULAR RECOGNITION

KW - AQUEOUS-MEDIA

KW - SYNTHETIC RECEPTORS

KW - AMMONIUM CATIONS

KW - CAVITANDS

KW - INCLUSION

KW - GUEST

KW - ACETYLCHOLINE

KW - CHEMOSENSOR

KW - DERIVATIVES

U2 - 10.1021/ja038823m

DO - 10.1021/ja038823m

M3 - Article

VL - 126

SP - 2870

EP - 2876

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

ER -